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Tuning protonation states of tripelennamine antihistamines by cucurbit[7]uril
Author(s) -
Saleh Na'il,
AlHandawi Marieh B.,
Bufaroosha Muna S.,
Assaf Khaleel I.,
Nau Werner M.
Publication year - 2016
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3504
Subject(s) - chemistry , protonation , cucurbituril , antihistamine , histamine , combinatorial chemistry , stereochemistry , molecule , computational chemistry , organic chemistry , supramolecular chemistry , pharmacology , medicine , ion
The formation of host–guest complexes of cucurbit[7]uril (CB7) with the antihistamine drug tripelennamine (TRP) was studied by optical and NMR spectroscopy. The experimental and computational results are consistent with inclusion of a single TRP molecule in CB7. Addition of CB7 has tuned drug protonation states associated with (de)protonation of the ethyldimethylammonium and exocyclic nitrogens with an increase in the associated p K a values by 1.5 and 2.5 units, respectively. The incorporation of antihistamines drugs such as TRP in cucurbiturils could be utilized for switching their capability for selective binding to histamine H 1 ‐receptors, in the future. Copyright © 2015 John Wiley & Sons, Ltd.
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